#------------------------------------------------------------------------------
#$Date: 2020-03-25 04:49:18 +0200 (Wed, 25 Mar 2020) $
#$Revision: 249689 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/01/7240170.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7240170
loop_
_publ_author_name
'Foyle, Émer M.'
'White, Nicholas G.'
_publ_section_title
;
 Anion templated crystal engineering of halogen bonding tripodal
 tris(halopyridinium) compounds
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00241K
_journal_year                    2020
_chemical_formula_moiety         'C42 H57 Br3 N3 O3, C2 H3 N, 3(Br)'
_chemical_formula_sum            'C44 H60 Br6 N4 O3'
_chemical_formula_weight         1172.36
_space_group_crystal_system      trigonal
_space_group_IT_number           147
_space_group_name_Hall           '-P 3'
_space_group_name_H-M_alt        'P -3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-18 deposited with the CCDC.	2020-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   16.57730(10)
_cell_length_b                   16.57730(10)
_cell_length_c                   10.49130(10)
_cell_measurement_reflns_used    17486
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6810
_cell_measurement_theta_min      4.1920
_cell_volume                     2496.82(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      9.00  49.00   1.00    3.00    --   36.95  19.00  60.00   40
  2  ω    -30.00  35.00   1.00    3.00    --   36.95 -38.00 -90.00   65
  3  ω    -32.00  31.00   1.00    3.00    --   36.95 -19.00-150.00   63
  4  ω     30.00  76.00   1.00    3.00    --   36.95 -99.00-120.00   46
  5  ω      9.00  36.00   1.00    3.00    --   36.95 -99.00 120.00   27
  6  ω     22.00  51.00   1.00    3.00    --   36.95 -57.00   0.00   29
  7  ω    -21.00  18.00   1.00    3.00    --   36.95 -77.00 -90.00   39
  8  ω     -6.00  19.00   1.00    3.00    --   36.95 -57.00   0.00   25
  9  ω     29.00  64.00   1.00    3.00    --   36.95  57.00 120.00   35
 10  ω     21.00  47.00   1.00    3.00    --   36.95  57.00   0.00   26
 11  ω     32.00  96.00   1.00    3.00    --   36.95  38.00-120.00   64
 12  ω     54.00  80.00   1.00    3.00    --   36.95-125.00-180.00   26
 13  ω     57.00  85.00   1.00    3.00    --   36.95  19.00  60.00   28
 14  ω    -26.00  45.00   1.00    3.00    --   36.95 -57.00 120.00   71
 15  ω    -18.00  64.00   1.00    3.00    --   36.95 -77.00   0.00   82
 16  ω     42.00  88.00   1.00    3.00    --   36.95-125.00  90.00   46
 17  ω     44.00  73.00   1.00   15.00    --  111.00 -50.00-150.00   29
 18  ω    129.00 172.00   1.00   15.00    --  111.00  25.00 -90.00   43
 19  ω     42.00 135.00   1.00   15.00    --  111.00 -25.00-180.00   93
 20  ω     74.00 121.00   1.00   15.00    --  111.00 -50.00 -90.00   47
 21  ω     95.00 128.00   1.00   15.00    --  111.00  50.00 120.00   33
 22  ω     42.00 109.00   1.00   15.00    --  111.00-111.00-150.00   67
 23  ω     67.00  93.00   1.00   15.00    --  111.00 -38.00  90.00   26
 24  ω    145.00 170.00   1.00   15.00    --  111.00  38.00  90.00   25
 25  ω     62.00  90.00   1.00   15.00    --  111.00-172.00 118.00   28
 26  ω    101.00 137.00   1.00   15.00    --  111.00-172.00 118.00   36
 27  ω     43.00  91.00   1.00   15.00    --  111.00 -92.00  60.00   48
 28  ω     44.00 137.00   1.00   15.00    --  111.00 -77.00-150.00   93
 29  ω     97.00 134.00   1.00   15.00    --  111.00 -72.00 -13.23   37
 30  ω     56.00  97.00   1.00   15.00    --  111.00-111.00 -60.00   41
 31  ω     98.00 170.00   1.00   15.00    --  111.00  12.00 150.00   72
 32  ω     75.00 109.00   1.00   15.00    --  111.00-111.00  90.00   34
 33  ω    132.00 161.00   1.00   15.00    --  111.00 111.00  60.00   29
 34  ω     70.00 122.00   1.00   15.00    --  111.00 -64.00  30.00   52
 35  ω     44.00  91.00   1.00   15.00    --  111.00 -50.00  90.00   47
 36  ω    151.00 178.00   1.00   15.00    --  111.00  38.00   0.00   27
 37  ω     87.00 157.00   1.00   15.00    --  111.00 -12.00 -90.00   70
 38  ω     43.00  69.00   1.00   15.00    --  111.00 -12.00 -90.00   26
 39  ω     63.00 109.00   1.00   15.00    --  111.00-111.00 150.00   46
 40  ω     85.00 110.00   1.00   15.00    --  111.00-115.00-100.00   25
 41  ω     42.00  67.00   1.00   15.00    --  111.00-115.00-100.00   25
 42  ω     58.00  84.00   1.00   15.00    --  111.00 -92.00-150.00   26
 43  ω     92.00 125.00   1.00   15.00    --  111.00  38.00   0.00   33
 44  ω    150.00 176.00   1.00   15.00    --  111.00  50.00 150.00   26
 45  ω    102.00 128.00   1.00   15.00    --  111.00  50.00 150.00   26
 46  ω     95.00 124.00   1.00   15.00    --  111.00  50.00-150.00   29
 47  ω     84.00 109.00   1.00   15.00    --  111.00-111.00  60.00   25
 48  ω     96.00 134.00   1.00   15.00    --  111.00  38.00  90.00   38
 49  ω     62.00 120.00   1.00   15.00    --  111.00 178.00-180.00   58
 50  ω     68.00 125.00   1.00   15.00    --  111.00 -38.00-120.00   57
 51  ω     58.00  94.00   1.00   15.00    --  111.00 -92.00 -90.00   36
 52  ω     84.00 109.00   1.00   15.00    --  111.00-111.00 -30.00   25
 53  ω     53.00 144.00   1.00   15.00    --  111.00 -12.00  90.00   91
 54  ω     69.00  95.00   1.00   15.00    --  111.00 -64.00 -60.00   26
 55  ω     75.00 100.00   1.00   15.00    --  111.00 -77.00   0.00   25
 56  ω     75.00 104.00   1.00   15.00    --  111.00 -92.00 -30.00   29
 57  ω     84.00 109.00   1.00   15.00    --  111.00-111.00 120.00   25
 58  ω    115.00 141.00   1.00   15.00    --  111.00  77.00 120.00   26
 59  ω     58.00  83.00   1.00   15.00    --  111.00 -64.00 150.00   25
 60  ω     41.00  67.00   1.00   15.00    --  111.00-111.00  60.00   26
 61  ω     96.00 122.00   1.00   15.00    --  111.00 -64.00-150.00   26
 62  ω     72.00  97.00   1.00   15.00    --  111.00 -64.00  90.00   25
 63  ω     77.00 102.00   1.00   15.00    --  111.00 -92.00 150.00   25
 64  ω     58.00  97.00   1.00   15.00    --  111.00 -32.00 -17.98   39
 65  ω     78.00 103.00   1.00   15.00    --  111.00 -80.00 -98.55   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0365277000
_diffrn_orient_matrix_UB_12      -0.0608125000
_diffrn_orient_matrix_UB_13      0.0588503000
_diffrn_orient_matrix_UB_21      0.0976813000
_diffrn_orient_matrix_UB_22      0.0864755000
_diffrn_orient_matrix_UB_23      0.0125946000
_diffrn_orient_matrix_UB_31      -0.0252307000
_diffrn_orient_matrix_UB_32      0.0185688000
_diffrn_orient_matrix_UB_33      0.1339105000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            31656
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.695
_diffrn_reflns_theta_min         4.214
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.36a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_description       needle
_exptl_crystal_F_000             1172
_exptl_crystal_recrystallization_method
'diffusion of diethyl into acetonirtile'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.021
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1390
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3110
_reflns_number_total             3363
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00241k2.cif
_cod_data_source_block           emf-4-58g
_cod_original_cell_volume        2496.82(4)
_cod_database_code               7240170
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C42H57N3O3Br6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.580
_shelx_estimated_absorpt_t_min   0.169
_reflns_odcompleteness_completeness 98.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H16A(0.33333) H16B(0.33333) H16C(0.33333)
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B),
 C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C3(H3), C2(H2)
3.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C14(H14A,H14B,H14C)
;
_ins_header
;
TITL EMF-4-58g in P-3 
REM P-3 (#147 in standard setting)
CELL 1.54184  16.577268  16.577268  10.491264  90.0000  90.0000 120.0000
ZERR    3.00   0.000148   0.000148   0.000085   0.0000   0.0000   0.0000
LATT  1
SYMM -y, x-y, z 
SYMM -x+y,-x, z 
SFAC C H N O Br
UNIT 126.00 171.00 9.00 9.00 18.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.190
_oxdiff_exptl_absorpt_empirical_full_min 0.455
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 1.07874(2) 0.45326(2) 0.80783(3) 0.03255(16) Uani 1 1 d . . . . .
Br1 Br 1.14973(2) 0.75155(2) 0.67520(4) 0.04588(17) Uani 1 1 d . . . . .
O1 O 0.78088(14) 0.25688(14) 0.85428(19) 0.0262(4) Uani 1 1 d . . . . .
N1 N 0.90588(15) 0.51301(15) 0.7478(2) 0.0213(4) Uani 1 1 d . . . . .
N2 N 0.666667 0.333333 0.4846(4) 0.0365(10) Uani 1 3 d S T P . .
C8 C 0.72519(17) 0.29594(18) 0.8626(2) 0.0196(5) Uani 1 1 d . . . . .
C6 C 0.86753(16) 0.45493(17) 0.8655(2) 0.0210(5) Uani 1 1 d . . . . .
H6A H 0.896831 0.417308 0.876395 0.025 Uiso 1 1 calc R . . . .
H6B H 0.883790 0.495911 0.938687 0.025 Uiso 1 1 calc R . . . .
C7 C 0.76401(16) 0.39205(17) 0.8629(2) 0.0192(5) Uani 1 1 d . . . . .
C15 C 0.666667 0.333333 0.3751(6) 0.0338(11) Uani 1 3 d S T P . .
C1 C 0.8636(2) 0.4831(2) 0.6341(3) 0.0286(5) Uani 1 1 d . . . . .
H1 H 0.806533 0.428200 0.628866 0.034 Uiso 1 1 calc R . . . .
C5 C 0.98863(18) 0.59067(19) 0.7583(3) 0.0247(5) Uani 1 1 d . . . . .
H5 H 1.017074 0.609093 0.837688 0.030 Uiso 1 1 calc R . . . .
C4 C 1.0323(2) 0.6439(2) 0.6513(3) 0.0304(6) Uani 1 1 d . . . . .
C3 C 0.9907(2) 0.6155(2) 0.5337(3) 0.0358(6) Uani 1 1 d . . . . .
H3 H 1.019543 0.650182 0.461046 0.043 Uiso 1 1 calc R . . . .
C2 C 0.9049(2) 0.5341(2) 0.5253(3) 0.0349(7) Uani 1 1 d . . . . .
H2 H 0.875528 0.514061 0.446773 0.042 Uiso 1 1 calc R . . . .
C9 C 0.8174(2) 0.2483(2) 0.9778(3) 0.0369(7) Uani 1 1 d . . . . .
H9A H 0.766615 0.205419 1.032146 0.044 Uiso 1 1 calc R . . . .
H9B H 0.849422 0.308439 1.019755 0.044 Uiso 1 1 calc R . . . .
C16 C 0.666667 0.333333 0.2347(5) 0.0380(11) Uani 1 3 d S T P . .
H16A H 0.618284 0.344146 0.204200 0.057 Uiso 0.3333 1 calc GR . . A -1
H16B H 0.655854 0.274137 0.204200 0.057 Uiso 0.3333 1 calc GR . . A -1
H16C H 0.725863 0.381717 0.204200 0.057 Uiso 0.3333 1 calc GR . . A -1
C10 C 0.8828(3) 0.2133(3) 0.9562(4) 0.0550(10) Uani 1 1 d . . . . .
H10A H 0.932773 0.256232 0.900846 0.066 Uiso 1 1 calc R . . . .
H10B H 0.910078 0.211052 1.036982 0.066 Uiso 1 1 calc R . . . .
C11 C 0.8367(4) 0.1209(4) 0.8988(6) 0.0757(15) Uani 1 1 d . . . . .
H11A H 0.801627 0.121335 0.825057 0.091 Uiso 1 1 calc R . . . .
H11B H 0.792740 0.076711 0.959617 0.091 Uiso 1 1 calc R . . . .
C13 C 0.9689(8) 0.1419(8) 0.7537(10) 0.130(4) Uani 1 1 d . . . . .
H13A H 1.007196 0.205121 0.784487 0.156 Uiso 1 1 calc R . . . .
H13B H 1.010060 0.117120 0.738134 0.156 Uiso 1 1 calc R . . . .
C12 C 0.9048(7) 0.0869(6) 0.8565(9) 0.108(3) Uani 1 1 d . . . . .
H12A H 0.941145 0.088386 0.929832 0.130 Uiso 1 1 calc R . . . .
H12B H 0.868519 0.022681 0.828712 0.130 Uiso 1 1 calc R . . . .
C14 C 0.9294(13) 0.1463(10) 0.6327(11) 0.185(7) Uani 1 1 d . . . . .
H14A H 0.978592 0.186102 0.575459 0.277 Uiso 1 1 calc GR . . . .
H14B H 0.888454 0.170888 0.645379 0.277 Uiso 1 1 calc GR . . . .
H14C H 0.895069 0.084943 0.596827 0.277 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C9 113.5(2) . . ?
C1 N1 C6 121.2(2) . . ?
C5 N1 C6 116.9(2) . . ?
C5 N1 C1 121.5(2) . . ?
O1 C8 C7 120.5(2) . . ?
O1 C8 C7 118.0(2) . 3_665 ?
C7 C8 C7 121.4(2) . 3_665 ?
C7 C6 N1 113.74(19) . . ?
C8 C7 C8 118.6(2) . 2_655 ?
C8 C7 C6 120.7(2) . . ?
C8 C7 C6 120.6(2) 2_655 . ?
N2 C15 C16 180.0 . . ?
N1 C1 C2 119.9(3) . . ?
N1 C5 C4 120.2(2) . . ?
C5 C4 Br1 117.2(2) . . ?
C3 C4 Br1 123.1(2) . . ?
C3 C4 C5 119.7(3) . . ?
C4 C3 C2 118.9(3) . . ?
C1 C2 C3 119.7(3) . . ?
O1 C9 C10 108.8(3) . . ?
C11 C10 C9 111.9(4) . . ?
C10 C11 C12 113.9(6) . . ?
C14 C13 C12 118.1(12) . . ?
C13 C12 C11 114.6(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.887(3) . ?
O1 C8 1.370(3) . ?
O1 C9 1.467(4) . ?
N1 C6 1.498(3) . ?
N1 C1 1.346(3) . ?
N1 C5 1.336(3) . ?
N2 C15 1.150(8) . ?
C8 C7 1.388(3) . ?
C8 C7 1.407(3) 3_665 ?
C6 C7 1.498(3) . ?
C15 C16 1.473(8) . ?
C1 C2 1.382(4) . ?
C5 C4 1.388(4) . ?
C4 C3 1.376(5) . ?
C3 C2 1.390(5) . ?
C9 C10 1.479(5) . ?
C10 C11 1.458(8) . ?
C11 C12 1.556(9) . ?
C13 C12 1.468(14) . ?
C13 C14 1.447(15) . ?
